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The Annex

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About The Annex

One of Toronto’s oldest and most prestigious neighbourhoods, the Annex was a highly-coveted area when it was first constructed in the 1870s. It was almost immediately inhabited by members of the city’s elite—which is to say, those who could afford the gorgeous homes here.

To this day, heritage houses constructed of iconic red brick and stone are still standing in the neighbourhood. These high-quality structures offer visitors and residents a glimpse of Toronto’s past.

The Annex is also very conveniently located. It sits just west of one of Toronto’s most luxurious residential areas (Yorkville) and north of a designer shopping district along Bloor Street West (playfully referred to as “Mink Mile.”)

Who Lives Here

For quite some time, many of the Annex’s mansions were split up into separate apartments as affluent residents moved to newer areas outside the city’s core. For this reason, you’ll find many young people in the area, including students who attend the nearby University of Toronto.

Today, mansions in the Annex are once again being purchased by higher-income individuals—and revamped to suit their lifestyles. Today, you’ll find a great mix of people and cultures, from those who ride bicycles to those who drive Lamborghinis.

What's Great About It?

The convenience of living in the Annex is hard to beat. While many of the neighbourhood’s tree-lined side streets are peaceful and quiet, every corner of the Annex is relatively close to a major intersection or main street. In other words, buzz-worthy boutiques, restaurants, cafes, and bars are never far away.

In particular, this vibrant neighbourhood is known for its eateries, which serve diverse tastes. One of the clear favourites is Kinka Izakaya, a local hotspot for top-notch Japanese cuisine.

When you’re looking to spend a fun afternoon out, consider hitting the shops (BMV Books is a must-visit for lovers of literature) or catching a truly unique film at Bloor Hot Docs. Those looking to stay active will want to visit Niles Nadal JCC, a local community centre featuring a pool, running track, and more.

Lastly, the Annex is much loved by architecture buffs. With so many beautiful streets to explore, you’ll never tire of the gorgeous heritage homes here.

Schools

When it comes to schools in the Annex, the most popular elementary options are Huron Street Junior Public School and Palmerston Junior Public School (both of which are located on their namesake streets).

The Annex is also home to the famed all-boys private school Royal St. George’s College, which welcomes students between Grades 3 to 12.

Homes for sale in The Annex

Looking for listings in The Annex for sale? You’re only seeing some of the listings available here. To see them all, just click the ‘Signup’ or ‘Login’ links below.

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We have found a total of 199 listings, but only 175 are available for public display. To get instant access to all 199 listings, please .
1-12/175

  • 1-6 66 Avenue Road in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12002469

    1-6 66 Avenue Road Annex Toronto M5R 3N8
    Main Photo: 1-6 66 Avenue Road in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12002469

    1-6 66 Avenue Road Toronto M5R 3N8 Annex

    $7,500,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    C12002469
    Major Bus.:
    Medical/Dental
    Total Area:
    0 sq. ft.
    Once-in-a-lifetime investment opportunity. Prime Yorkville medical offices. Location does not get better than this. On the corner of Lowther/Avenue. Six fully tenanted commercial offices/medical offices. Complete first floor with auxiliary storage room in lower level. 12 underground parking spots. More details
    Listed by CHESTNUT PARK REAL ESTATE LIMITED
    LISTING DETAILS
    Tanya Crepulja
    Steven Fontes

  • Garden Home 2 10 Prince Arthur Avenue in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12243593

    Garden Home 2 10 Prince Arthur Avenue Annex Toronto M5R 1A9
    Main Photo: Garden Home 2 10 Prince Arthur Avenue in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12243593

    Garden Home 2 10 Prince Arthur Avenue Toronto M5R 1A9 Annex

    $6,950,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12243593
    Bedrooms:
    4
    Bathrooms:
    3
    An exceptional Garden Home now available at 10 Prince Arthur! The style and convenience of an Urban Bungalow - with almost 2,750 square feet of gracious interior space on a single level, surrounded by a private landscaped garden terrace all to yourself! Unequalled space steps to Avenue Road and Bloor in an intimate development of just 25 residences. 11 foot ceilings, expansive kitchen featuring Wolf and Sub-Zero appliances, 2 bedrooms with a den and office... this really feels like home. Developed by North Drive and designed by Richard Wengle with refined interiors from Brian Gluckstein and Michael London and featuring a very limited number of residences in a truly boutique building. Enjoy the comfort and convenience of 24-hour concierge, valet parking, private fitness facility, resident dining lounge with catering kitchen and courtyard sculpture garden designed by Janet Rosenberg. Located in the Annex, just steps from exceptional shopping, Yorkville's world-class dining, U of T, cultural institutions and the tranquil greenery of nearby parks, 10 Prince Arthur presents a rare blend of urban sophistication and neighborhood charm. **EXTRAS** A unique urban home. Wrap around garden with 3 distinct areas and 5 walk-outs from inside. Landscape lighting and irrigation. Includes secure, 2 car underground parking, storage and hst. More details
    Listed by RIGHT AT HOME REALTY
    LISTING DETAILS
    Tanya Crepulja
    Steven Fontes

  • Part of 128 Pears Avenue in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12023590

    Part of 128 Pears Avenue Annex Toronto M5R 1T2
    Main Photo: Part of 128 Pears Avenue in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12023590

    Part of 128 Pears Avenue Toronto M5R 1T2 Annex

    $6,723,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    C12023590
    Major Bus.:
    Retail Store Related
    Total Area:
    4,482 sq. ft.
    3-storey luxury freehold commercial component with ground-floor lobby, steps from busy intersection of Avenue Rd and Davenport Rd. Close proximity to Yorkville and to Rosedale Subway Station. Ideal for a wide range of uses including office, medical, and commercial uses. Shared access to elevator pursuant to Facilities Agreement. More details
    Listed by THE BEHAR GROUP REALTY INC.
    LISTING DETAILS
    Tanya Crepulja
    Steven Fontes

  • 18 Lowther Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12223307

    18 Lowther Avenue Annex Toronto M5R 1C6
    Main Photo: 18 Lowther Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12223307

    18 Lowther Avenue Toronto M5R 1C6 Annex

    $5,895,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12223307
    Bedrooms:
    4
    Bathrooms:
    4
    Situated on one of the city's most coveted streets, 18 Lowther Avenue blends modern living with timeless elegance. This three bedroom home featuring an open-concept main floor with over 3,200 sq. feet (above-grade) of light-filled living space throughout. The main floor boasts a large living room with soaring 10 ft ceilings and with spectacular solarium-style window opening up to the private garden patio, perfect for outdoor entertaining. The nice sized dining space flows in a gourmet chef's kitchen with large island, top of the line appliances and a beautiful bay window overlooking the streetscape.Ascend the stairs to the second floor where you will find a generous sized family room that could easily serve as a fourth bedroom. Walk down the hall to the large primary with five-piece ensuite, lots of closet space and big windows drawing in a ton of natural light. The third floor has a large bedroom with walk-in closet, washroom, cozy den/office and a third floor terrace with north facing views. The lower level features a third bedroom, washroom, laundry room and large crawl space perfect for storing seasonal things. Walk out to a private garden oasis and enjoy the convenience of a rare double garage. Just steps from the University of Toronto, the Royal Ontario Museum, and upscale shops and restaurants in Yorkville.Close to some of the city's best schools, galleries, and green spaces. More details
    Listed by ROYAL LEPAGE REAL ESTATE SERVICES HEAPS ESTRIN TEAM
    LISTING DETAILS
    Tanya Crepulja
    Steven Fontes

  • 404 10 Prince Arthur Avenue in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12241419

    404 10 Prince Arthur Avenue Annex Toronto M5R 1A9
    Main Photo: 404 10 Prince Arthur Avenue in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12241419

    404 10 Prince Arthur Avenue Toronto M5R 1A9 Annex

    $5,590,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12241419
    Bedrooms:
    3
    Bathrooms:
    3
    Now available at 10 Prince Arthur! This brand new 2 bedroom plus family room residence represents one of the final homes at this intimate development of just 25 residences. With occupancy already underway, now is the ideal time to secure this elegant suite providing almost 2,400 square feet of interior space with 10 foot ceilings, an expansive kitchen featuring Wolf and Sub-Zero appliances and a privileged south exposure with views over quiet Prince Arthur Avenue. Developed by North Drive and designed by Richard Wengle with refined interiors from Brian Gluckstein and Michael London and featuring a very limited number of residences in a truly boutique building. Enjoy the comfort and convenience of 24-hour concierge, valet parking, private fitness facility, resident dining lounge with catering kitchen and courtyard sculpture garden designed by Janet Rosenberg. Located in the Annex, just steps from exceptional shopping, Yorkville's world-class dining, U of T, cultural institutions and the tranquil greenery of nearby parks, 10 Prince Arthur presents a rare blend of urban sophistication and neighborhood charm. **EXTRAS** A unique urban home. 2 balconies, one from family room and one from primary bedroom. Includes secure, 2 car underground parking, storage and hst. More details
    Listed by RIGHT AT HOME REALTY
    LISTING DETAILS
    Tanya Crepulja
    Steven Fontes

  • 90 Madison Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12051367

    90 Madison Avenue Annex Toronto M5R 2S4
    Main Photo: 90 Madison Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12051367

    90 Madison Avenue Toronto M5R 2S4 Annex

    $5,369,490
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12051367
    Bedrooms:
    7
    Bathrooms:
    8
    Architectural Masterpiece Of Urban Design On One Of The Most Coveted Streets, In The Heart Of The Annex. Located On A Large 40 x 127 West Facing Lot, On A Premium Block. Retaining Its Turn Of The Century Character This Home Was Rebuilt To Reflect Modern Design And Traditional Warmth. A Spectacular Over 3700 sf New York Style Loft Was Seamlessly Added To A Traditional Annex Home Creating Approximately 7000 sf Living Space. This Lightfilled contemporary space with its soaring 3 storey west facing windows brings the outside into the inside of the home, and features fabulous Catwalks Connecting The 3 Levels And Spaces. An Elevator From The Lower Level Garage Connects The 4 Levels. The Space Is Open Yet There Is Privacy In The 4 Bedrooms. A Fabulous 2 Bedroom 2250 sf Separate Unit With a Walkout Lower Level Plus A 2 Bedroom Third Floor Unit Allow For Extra Income Or Extended Family Space. 4 - 5 Car Parking, Private Drive, Built In Garage. Exceptional Urban Living, Just Steps To Yorkville, Subway, Royal St Georges College, Huron Public, Mabin School, Rosedale Day School, UTS, U of T More details
    Listed by RE/MAX PROFESSIONALS INC.
    LISTING DETAILS
    Tanya Crepulja
    Steven Fontes

  • 102 277 Davenport Road in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12022688

    102 277 Davenport Road Annex Toronto M5R 1J9
    Main Photo: 102 277 Davenport Road in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12022688

    102 277 Davenport Road Toronto M5R 1J9 Annex

    $5,198,000 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    C12022688
    Total Area:
    3,663 sq. ft.
    One of the sexiest commercial spaces you will ever see. This architectural gem designed by Hariri Pontarini, 277 Davenport Rd is one of Yorkville's most desirable boutique luxury condominiums. Steps to the heart of Yorkville, Suite 102 delivers just shy of 3,700 sq. ft. of exquisite space, from the beautifully proportioned reception area to the open concept main floor with beautiful tall ceilings and dramatic double height ceiling draws the eye skyward towards the beautiful mezzanine level. Exeptional office/retail space zoned CR 2.0 for a variety of uses. Prime location, steps to the heart of Yorkville with superb exposure on Davenport between Bedford & Avenue Road. 2 Car parking, polished concrete floors, wheelchair accessible with ramp, 3 x 2 piece baths, ensuite laundry. 5 Minute walk to Dupont & Bay St. subway stations. More details
    Listed by SOTHEBY`S INTERNATIONAL REALTY CANADA and SOTHEBY'S INTERNATIONAL REALTY CANADA
    LISTING DETAILS
    Tanya Crepulja
    Steven Fontes

  • 1202 206 Bloor Street W in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12243091

    1202 206 Bloor Street W Annex Toronto M5S 1T8
    Main Photo: 1202 206 Bloor Street W in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12243091

    1202 206 Bloor Street W Toronto M5S 1T8 Annex

    $4,995,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12243091
    Bedrooms:
    3
    Bathrooms:
    3
    Sophisticated Luxury in the Heart of Yorkville. Welcome to Museum House, an iconic 19-storey landmark residence in the heart of Bloor-Yorkville, offering boutique luxury living at its finest. This breathtaking 3-bedroom, 3-bathroom suite spans over 2,500 square feet of elegantly appointed space, with direct elevator access opening into your private residence. Enjoy uninterrupted southern CN Tower city views, each room framed by floor-to-ceiling windows that flood the home with natural light. The expansive open-concept living and dining areas are perfect for entertaining, while the custom kitchen boasts a large island, premium appliances, integrated wine refrigeration, and a sunlit breakfast area. The primary suite is a true retreat, featuring a spa-inspired ensuite and a spacious walk-in closet. The versatile third bedroom easily transforms into a refined home office. With soaring ceilings, impeccable finishes, and an unmatched location steps from Yorkvilles finest restaurants, designer boutiques, art galleries, and cultural institutions - this is urban luxury redefined. More details
    Listed by HARVEY KALLES REAL ESTATE LTD.
    LISTING DETAILS
    Tanya Crepulja
    Steven Fontes

  • 133 Pears Avenue in Toronto: Annex Condo Townhouse for sale (Toronto C02) : MLS®# C12218903

    133 Pears Avenue Annex Toronto M5R 1T3
    Main Photo: 133 Pears Avenue in Toronto: Annex Condo Townhouse for sale (Toronto C02) : MLS®# C12218903

    133 Pears Avenue Toronto M5R 1T3 Annex

    $4,995,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12218903
    Bedrooms:
    3
    Bathrooms:
    4
    Refined Urban Living At 133 Pears Avenue Where The Annex Meets Yorkville. The Largest Of Only Five Exclusive Town Homes. Enjoy All The Services And Amenities Of Its Upscale Adjoining Tower Residence Located Within The Prestigious Pears On The Avenue Community. Richly Appointed Designer Palette. This Residence Features A Magnificent Rooftop Terrace With A Fire Table, Bbq, Wood Floors, A Great Place to Entertain With An Abundance Of Blue Skies. Multiple Seating Areas And Balconies, Den Which Can Be Easily Transformed To A Third Bedroom, Multiple Walkouts, 10-Foot Ceilings, Ample Storage, Custom Built-Ins And Millwork, Designer And Builders Upgrades, Chef's Kitchen With Top Tier Miele Appliances. Private Elevator, Heated Floors, Smart Home Features - Work At Home Environment And Spacious Principal Rooms. A Luxurious Primary Suite With A Spa-Like Ensuite, Balcony And Large Walk-In Closet. Enjoy Two Underground Parking Spaces only a few steps from your door, Just Steps From Top-Tier Dining, Yorkville Shops and Walks and TTC. More details
    Listed by RE/MAX REALTRON BARRY COHEN HOMES INC.
    LISTING DETAILS
    Tanya Crepulja
    Steven Fontes

  • 37 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12254763

    37 Madison Avenue Annex Toronto M5R 2S2
    Main Photo: 37 Madison Avenue in Toronto: Annex Commercial for sale (Toronto C02) : MLS®# C12254763

    37 Madison Avenue Toronto M5R 2S2 Annex

    $4,988,888 /For Sale
    Commercial
    Status:
    Active
    MLS® Num:
    C12254763
    Total Area:
    7,262 sq. ft.
    Offered at $4,988,888, 37 Madison Avenue is a rare opportunity to own a landmark building in the heart of Toronto's prestigious Annex/Yorkville corridor. Designed by Edward James Lennox, architect of Casa Loma and Old City Hall, this three-storey, approx. 6,000 sq. ft. property blends Gothic, Queen Anne, and Edwardian influences with exceptional presence. Currently configured as elegant office space with 12 executive offices, 4 bathrooms, and 8 rear parking spaces, the building offers outstanding flexibility for a head office, wellness clinic, gallery, boutique hotel, or studio. A striking façade, historic character, and prime location just steps from Bloor Street, two subway lines, U of T, and Yorkville make this a truly unique commercial offering. More details
    Listed by RE/MAX REALTRON REALTY INC.
    LISTING DETAILS
    Tanya Crepulja
    Steven Fontes

  • 700 38 Avenue Road in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12210832

    700 38 Avenue Road Annex Toronto M5R 2G2
    Main Photo: 700 38 Avenue Road in Toronto: Annex Condo Apartment for sale (Toronto C02) : MLS®# C12210832

    700 38 Avenue Road Toronto M5R 2G2 Annex

    $4,980,000
    Residential Condo & Other
    Status:
    Active
    MLS® Num:
    C12210832
    Bedrooms:
    3
    Bathrooms:
    4
    Enjoy the luxury of living in The Prince Arthur at a prime Yorkville location. Along with providing valet parking, the attentive 24-hour concierge and valets create a sense of secure privacy as they manage access to condo areas. Situated in the south tower, this corner suite has a wonderful layout featuring 3 bedrooms in two wings with 4 bathrooms, 2 balconies, 3 parking spaces, 2 lockers and many built-ins. The suite is approximately 3115 square feet, with desirable western views, peaceful northern views from the primary bedroom and tandem sitting room suite and additional south views in the kitchen and dining room. Enter through wide double doors to an inviting foyer with a large closet, continuing into the large welcoming living room, the focus of the suite. As you enter, you find an elegant, wood paneled library through double doors on the right. On the left a second set of double doors leads to a separate, formal dining room which is also accessible from a beautiful modern kitchen with thoughtful design and eat-in area. The northern wing features a primary bedroom with a relaxing tandem sitting room, ensuite bathroom plus his and her closets. This wing includes a second bedroom, ensuite and sitting/office area with a walk-out to a west-facing balcony. The third/guest bedroom and ensuite are in the south wing next to the kitchen and powder room. Marvelous amenities include an exercise room, two well appointed party rooms each with open balconies (one overlooking Yorkville), sauna, theatre and library. Generous ensuite laundry area with laundry sink. Embrace the adventure and excitement of living in the cultural heart of Toronto. More details
    Listed by SUTTON GROUP OLD MILL REALTY INC.
    LISTING DETAILS
    Tanya Crepulja
    Steven Fontes

  • 67 Madison Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12233526

    67 Madison Avenue Annex Toronto M5R 2S3
    Main Photo: 67 Madison Avenue in Toronto: Annex House for sale (Toronto C02) : MLS®# C12233526

    67 Madison Avenue Toronto M5R 2S3 Annex

    $4,795,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    C12233526
    Bedrooms:
    7
    Bathrooms:
    5
    Set on one of Toronto's most picturesque, tree-lined streets, this spectacular 3-storey Victorian blends architectural heritage with refined modern living. Built in 1895 and beautifully restored in 2012 with exceptional attention to detail and craftsmanship, the home offers an open, airy, and grand sense of space from front to rear. The main level, w/soaring 10 ft. ceilings, features a welcoming foyer, elegant living room w/leaded glass windows and a tiled gas fireplace, and a formal dining room w/its own gas fireplace. Both principal rooms are richly appointed with wainscotting, mouldings, and period millwork that speak to the home's heritage character. Herringbone-patterned hardwood floors run throughout, setting an elegant tone. The heart of the home is the show-stopping kitchen with ceiling-height cabinetry, stone counters, & stainless steel appliances. A striking oversized counter w/bar seating anchors the space, overlooking the family room for seamless flow. A breakfast room/den w/built-in banquette offers a tucked-away workspace or casual dining nook, & powder room completes the level. The second floor, w/9 ft. high ceilings, is home to the primary suite w/ walk-in closet & spa-inspired 5-pc ensuite. A second bedroom w/double windows and a third bedroom share access to a semi-ensuite 4-piece bath. The third level includes two more bedrooms w/angled ceilings & skylights, plus a shared bath and second 3-pc ensuite perfect for teens and guests. One bedroom opens to the expansive sundeck, a serene retreat among the treetops. The lower level includes a rec room, two bedrooms, two full baths, den, laundry, & storage. A legal front pad parking space adds convenience, while the lush rear garden enhances the homes exceptional outdoor appeal. Inside, the thoughtfully designed interior reflects an unwavering commitment to comfort and quality. A rare find in the Annex just steps to U of T, the ROM, Bloor Street, Yorkville, and the subway. More details
    Listed by SOTHEBY'S INTERNATIONAL REALTY CANADA
    LISTING DETAILS
    Tanya Crepulja
    Steven Fontes
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Data was last updated July 3, 2025 at 02:15 AM (UTC)
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